However an old ex from school contacted me recently and we have been chatting,we didn't end on a bad note, just didn't work out, we grew apart but it was a pretty long relationship and I would love to connect but have always felt awkward about friendship with exes. It always felt like bad idea.

My friend Todd tries to be friends with his ex girlfriends, but then there are still residual feelings at times on their part, and sometimes they reject him and he gets sad because he once cared about them or sometimes they go to dinner and have wine....then he doesn't call them again the morning after. Todd just said he friended his ex Ashley on Facebook.... just to say hi, then he said she barely had anything to say to him, I recall that it ended badly with them. He claims he doesn't like to throw people away, and that I am far too quick to throw people aside, but I think it can be foolish.

When I broke up with my ex, we both said that it would be a shame to loose the friendship as well, she said this was a reason she did not want to break up.

We broke up 2 years ago, but we still see eachother regularly (at least once a month) for coffee or we go sailing or canoeing for the day.

For us, it is not awkward, it is good to have a friend you see regularly, and who knows you so well, that you can explain any issues you have in your daily live with, knoiwing that they understand why some things are a problem for you. I am glad I have this friendship and I wouldn't miss it for the world.

I think there are too many variables to make any kind of blanket statement - essentially its a case by case basis on whether it will out.

That said, IMO friendships work best when there's been a significant "cooling off" period of no, or virtually no, contact. This way each person has time to move on, heal, and start over (either in new relationships or being happy being alone). And a key to a successful friendship is neither person still longing for the other.

I am friends with some ex's, polite and wish no evil upon but not friends with others, some I wish no evil on but I'm not friends with anyway, and at least one I actively think is a bad person at his core and one I'm kinda embarrassed about and would rather not be friends because I'd feel icky.

I think that as long as you remember why you broke up with that ex in the first place and have no desire to have a further romantic relationship, it's fine to be friends. However, you are nostalgic and want to get back with that ex, then you don't need to be friends.

Of course this is colored by the fact that my husband just told me he wants to have a particular friend of his who he used to date in high school as a "scrabble-buddy"

I am FB friends with loads of exes. They are exes for a reason: they were not what I wanted for a spouse and/or father of my children. But they are still great guys.. and most of them are married now (or have been).

My DH has no problem with me being friends with them. He knows who is number one in my heart.

Boundaries are always good. Don't flirt, don't expect them to be anything like what you think they should be (just shake your head when they say or do something dumb) and be happy/sad/mad for them when they need you to be (just like if they were just a friend).

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I think that as long as you remember why you broke up with that ex in the first place and have no desire to have a further romantic relationship, it's fine to be friends. However, you are nostalgic and want to get back with that ex, then you don't need to be friends.

Of course this is colored by the fact that my husband just told me he wants to have a particular friend of his who he used to date in high school as a "scrabble-buddy"

What a nerve! I can't believe he said that to you, what on earth made him think that was an acceptable thing to think, let alone say out loud?

I think that as long as you remember why you broke up with that ex in the first place and have no desire to have a further romantic relationship, it's fine to be friends. However, you are nostalgic and want to get back with that ex, then you don't need to be friends.

Of course this is colored by the fact that my husband just told me he wants to have a particular friend of his who he used to date in high school as a "scrabble-buddy"

Wow, your husband wanting to have sex with an ex is pretty different to being friends with an ex. Unless you live in an open relationship that is totally unacceptable.

I think that as long as you remember why you broke up with that ex in the first place and have no desire to have a further romantic relationship, it's fine to be friends. However, you are nostalgic and want to get back with that ex, then you don't need to be friends.

Of course this is colored by the fact that my husband just told me he wants to have a particular friend of his who he used to date in high school as a "scrabble-buddy"

What a nerve! I can't believe he said that to you, what on earth made him think that was an acceptable thing to think, let alone say out loud?

It came up while we were discussing the fact that I am going to be out of town for an extended period of time in order to care for some relatives. This is about the 3rd time he's mentioned this particular woman and sounded serious. I let her (we're friends, though not super close) know what was going on in a "don't let him convince you I'm ok with this" type of conversation.

He does and says a lot of things that fall on the spectrum between "a little odd" and "batpoop insane". But this is an etiquette forum, not a relationships forum, so none of the topics here really apply to him. LOL.

Wow, your husband wanting to have sex with an ex is pretty different to being friends with an ex. Unless you live in an open relationship that is totally unacceptable.

I was concerned when he said he wanted to be friends with her, but she seems like a good person. She has a child with someone else, and seems to be more focused on raising her son and working on her relationship with her son's father than on running around stealing other people's men.

Oh, he asked me about an open relationship. I flat-out told him that the ONLY way I would even consider an open relationship is if our relationship was strong first. PLUS he wants it to only be open on his side! He gets jealous when I work late night shifts with a male manager (but not with a female).

Wow, your husband wanting to have sex with an ex is pretty different to being friends with an ex. Unless you live in an open relationship that is totally unacceptable.

I was concerned when he said he wanted to be friends with her, but she seems like a good person. She has a child with someone else, and seems to be more focused on raising her son and working on her relationship with her son's father than on running around stealing other people's men.

Oh, he asked me about an open relationship. I flat-out told him that the ONLY way I would even consider an open relationship is if our relationship was strong first. PLUS he wants it to only be open on his side! He gets jealous when I work late night shifts with a male manager (but not with a female).

Sorry if I messed up the quotes, but I'm new at this

My goodness. I don't know what to say to that, except that there are a lot of red flags. In your place, I would be having very strong words. An open relationship on his side only? Yeah, sure

I've found that most men are all for having an open relationship ... until they find out that having an open relationship means that BOTH parties get to have lovers!

There were strong words, words that went something like, "I am going to take care of my relatives who are ill. By the time I return, please have selected a counselor for us to go see, since we clearly need professional help." He says I'm evil for making him choose the counselor ... wierdo! I'm just glad that I have enough self-esteem not to buy into his chauvinistic games.

I've found that most men are all for having an open relationship ... until they find out that having an open relationship means that BOTH parties get to have lovers!

I have never found this in any relationship I've been.

I'm glad you've got something planned though.

Nor have I.

There do seem to be people (not all of them male) who want one set of rules for them, and a more restrictive set for their spouses/partners. And it happens in this context, too.

Back to OP: open relationships only work if both/all the people involved are comfortable with that, and in my experience/observations, have to be willing and able to talk to each other. (Not necessarily details of Scrabble with other people, but the emotional situation and logistics of time spent with each other and with other people.) It's past the point where her husband should have either dropped the subject and accepted that she wants a monogamous marriage, or told her explicitly that he wasn't prepared to continue that way, and asked whether he should be looking for a marriage counselor or arranging for an amicable divorce? Not kept asking for something that she has made plain she doesn't want. That would be obnoxious if it was about a weekend in the Poconos or replacing the couch, and this is higher stakes.

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Any advice that requires the use of a time machine may safely be ignored.